Illinois State Police said they were notified of a possible shooting and crash in the westbound lanes of I-290 at about 12:03 a.m.
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The crash involved two cars and a bullet hole could be seen on one of them.
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State troopers initially located an unoccupied vehicle on I-290 at Ashland Avenue. A second vehicle was then located at Damen Avenue.
The driver of the second vehicle was shot and pronounced dead at the scene, police said.
Two other people in the car were transported to hospitals with gunshot injuries, police said. Police said two other people in the second car were not injured.
The incident forced police to shut down the outbound Eisenhower at Ashland Avenue for hours, with lanes reopening at about 7:20 a.m. The motive behind the shooting remains unclear.